The 350-year old Port Annapolis offers both fascinating history and modern fun. The old brick sidewalks recall the days when Thomas Jefferson and George Washington strolled the streets, and Annapolis was capital of the United States. The city contains some of the country's nicest buildings from the 17th and 18th Centuries. It is the home of the 1696 St. John's College, the US' third oldest school of higher learning. It is also home of a beautiful waterfront where sailboat races and luxury yachts make it America's Sailing Capital. Whether taking a walking tour or a sightseeing cruise, Port Annapolis is one of America's most charming cities.

Port Annapolis has a humid subtropical climate with hot summers and cool winters. Its low elevation and location close to Chesapeake Bay moderate the temperatures compared to inland locations. Precipitation is fairly evenly distributed throughout the year, averaging about 3.7 inches (93.8 mm) per month. Temperatures range from an average high of 32°C (90°F) in July to an average low of -1°C (31°F) in January.

The wonderful Maryland State House is both the center for the State's government and a popular tourist destination. Capitol of the United States from November 1783 to August 1784, it is the oldest state house in the United States that is still used for legislative purposes. Open from 9am until 5pm all year (except Christmas and New Year's Day), self-guided tour information is available on the first floor Office of Interpretation. Visitors can also arrange appointments for special curator tours of the building and the artwork it contains. While tours are free, donations are appreciated.

Port Annapolis' Sandy Point State Park is about 19kilometers (12 miles) from downtown. Visitors can swim, crab, fish, boat, or windsurf at the beach while viewing the Chesapeake Bay Bridge. They can also picnic, hike, view wildlife, and visit historic sites. Open all year, the 786-acre park is located on the Bay's northwestern shore. The park offers boat rentals and contains a marina store. It is in an ideal location to see a wide range of waterfowl. From April until October, this Port Annapolis park is open from 6am until sunset. Other times of year, the park opens at 7am and closes around sunset. It is open all the time for fishing from January through November and for boating all year.

Port Annapolis' historic district is easy to tour by food. Guides from the Capital City Colonials wear period clothing as they explain Port Annapolis's history and buildings and the golden age of the colonial period as well as local culture and cuisine. Visitors can choose from a range of tours that include Annapolis-in-an-Hour, the Annapolis Food and History Tour, Women of Annapolis, Colonia Gossip, Washington's Resignation, and Grand Houses.

The popular Historic District 101 tour includes visits to several historic homes in Port Annapolis, the 1696 St. John's College, the late 17th Century Saint Anne's Church, the colonial kitchen of the Hammond-Harwood House, the Government House, and Maryland's State House. Separate tours visit the 1738 Jonas Green House that was the print shop and publisher of the Maryland Gazette and the Sands House that contains articles left by six generations of the family who owned the home for more than 237 years.

As America's Sailing Capital, Port Annapolis offers many opportunities for sailing adventures and tours. Schooner Windwood Cruises has two beautiful 22.6-meter (74-foot) schooners on which travelers can help sail or sit back and enjoy the experience. Sailing from Port Annapolis' historic waterfront, the schooners pass the Naval Academy on their way into Chesapeake Bay. The Woodwind features two-hour sailing cruises to specific locations like the Eastern Shore, lighthouses, and waterfront crab houses. Winwood II hosts private charters for companies and social events. One program involves a team-building exercise where a "guest" crew learns how to sail and race the schooners. Beginning in May, sunset sails are popular. Races between the two schooners are held during the boating season where passengers can participate.